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Date of Award


Document Type

Dissertation - Pacific Access Restricted

Degree Name

Doctor of Philosophy (Ph.D.)



First Advisor

Paul Gross

First Committee Member

Patrick Jones

Second Committee Member

Xiaoling Li

Third Committee Member

Vyacheslav Samoshin

Fourth Committee Member

Donald Wedegaertner


C-glycosides play important roles in biological processes. Synthetic efforts to prepare carbohydrate mimetics—C-glycosides were undertaken. This thesis introduces the total syntheses of C-glycosides by starting with two cycloaddition reactions. The [4+2] reaction of 1,3-pentadiene with glyoxylic acid and subsequent reactions afforded five C-pyranosides. The [4+3] cycloaddition of furan and pentachloroacetone and subsequent reactions provided C-furanosides and C-pyranosides. A new type of C-disaccharide mimetic coupled by an amide bond was synthesized. This thesis describes how bromolactonization, stereoselective Beckmann rearrangement and stereoselective dechlorination were used in a new way to fulfill the research goal. This dissertation provides efficient ways to synthesize carborhydrate mimetics from cheap, easily available non-natural materials.




9780493646251 , 0493646256

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